When you win the lottery jackpot, where is the first luxurious place you’d go? How about Hawaii, where the cultural festivities and sprawling beaches have attracted visitors for decades? Imagine stretching out in the sun with the sound of the ocean all around you, or sitting by torchlight and enjoying cultural dance performances and a feast of scrumptuous seafood.

Need more help imagining this trip? We’ve put together a 3-day itinerary for the island of Oahu, where a lottery winner can experience all that Hawaii has to offer.

Day 1

Blue Skies of Oahu Circle Island Helicopter Tour

bird's eye view of Oahu

Kickstart your trip by taking to the skies and experiencing Oahu like few people have. As you soar over the Hawaiian islands, you’ll see the crystal blue waters of Hanauma Bay, the white sands of Waimanalo Beach, and the coral reefs of Kaneohe Bay. You’ll even catch a glimpse of historic sites like Pearl Harbor, the Arizona Memorial, and the Battleship Missouri.

Lunch at Tiki’s Grill & Bar

tropical drinks

Now that you’ve worked up an appetite, it’s time to satisfy yourself with a classic Hawaiian meal. With the charm and aesthetic of ’50s and ’60s tiki bars, Tiki’s Grill & Bar features palm wood flooring and fishnet decor while offering the best flavors and ingredients of the island. Popular dishes include Calamari Katsu, Kalua Pig Quesadillas, and Tiki’s Famous Coconut Shrimp.

Majestic Waikiki Sunset Dinner Cruise

sunset cruise in Waikiki

Enjoy a Hawaiian sunset aboard an evening cruise, with a buffet dinner and live music. On Friday evenings, you can watch a brilliant fireworks display off the Waikiki coastline.

Day 2

Swimming with Dolphins at Dolphin Quest Oahu

a woman giving a kiss to a dolphin

Swim with the dolphins and their trainers, and have an experience you won’t soon forget. These friendly and intelligent aquatic creatures would love to pose for a picture and maybe even give you a kiss on the cheek!

Seafood Dining at Morimoto Waikiki

cheesecake at Morimoto Waikiki

A multi-award-winning restaurant, Morimoto Waikiki offers dishes made with locally grown fruits and vegetables as well as a constantly changing selection of fresh seafood options. The owner, Iron Chef Masaharu Morimoto, delivers his take on many traditional Hawaiian delicacies. Whatever you try, you’re sure to enjoy the meal.

Parasailing at Waikiki Beach

a couple parasailing on vacation

If you’re ever wanted to fly, Hawaiian parasailing is the closest you can get without sprouting wings. This thrilling adventure is not for the faint of heart—but it’s definitely worth it! Choose a water touchdown for an added splash.

Day 3

Oceanfront Brunch at Orchids

brunch at a restaurant

A perfect blend of casual and elegant, Orchids is a highly rated oceanfront restaurant in the Halekulani hotel. Drop by for their Sunday Brunch, which has been called “Oahu’s Best Brunch” by Honolulu Magazine.

North Shore Horseback Riding at Gunstock Ranch

horseback riding on the beach

Go for a leisurely trot along the base of the beautiful Ko’olau Mountain Range with experienced riders as your guide. Gunstock Ranch will introduce you to Oahu’s stunning sites along Kaneohe Bay to the North Shore.

Ali’i Luau Buffet Dinner at the Polynesian Cultural Center

Hawaiian luau dish

No trip to Hawaii is complete without a luau! The award-winning Ali’i Luautakes place outside, against a backdrop of tranquil waterfalls and lush gardens. Dine on traditional Hawaiian dishes like steam tropical fish, shoyu glazed chicken, lomilomi salmon, and more.

Thrilling Evening Show at the Polynesian Cultural Center

Polynesian fire dancers

Cap off your visit by watching a spectacular night show presented by the Polynesian Cultural Center. It features over 100 Polynesian natives, special effects, and surround sound. As a spectator, you can expect fire dancing, rhythmic music, amazing animated visuals—and an evening you’ll cherish for a long time.

Now when you win the Powerball jackpot, you’ll know how to spend your first weekend as a multi-millionaire. Aloha, and happy travels!

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